One-electron oxidation of aromatic hydrocarbons

Marcoux, Lynn; Fritsch, John M.; Adams, Ralph N.

doi:10.1021/ja00999a005

Cited by 54 publications

(22 citation statements)

References 6 publications

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“…Rh 2 (S-TCPTTL) 4 -catalyzed cyclopropanation of styrene with α-nitro-α-diazo para-methoxyacetophenone. 63 Charette and coworkers [77][78][79][80] described the enantioselective formation of 1,1-cyclopropane diesters via Rh 2 (S-NTTL) 4 catalyzed cyclopropanation of olefins (Scheme 17). They were the first to elaborate the concept of the trans-directing ability of the amide groups in Rh(II)-catalyzed cyclopropanation reactions which provided a solution for the stereoselective synthesis of 1,1-dicarboxycyclopropane derivatives.…”

Section: Dirhodium(ii) Catalysts Derived From N-protected Amino Acid mentioning

confidence: 99%

Chiral Dirhodium(II) Carboxylates and Carboxamidates as Effective Chemzymes in Asymmetric Synthesis of Three‐Membered Carbocycles

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Ghanem

2014

Chirality

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Section: Dirhodium(ii) Catalysts Derived From N-protected Amino Acid mentioning

confidence: 99%

Chiral Dirhodium(II) Carboxylates and Carboxamidates as Effective Chemzymes in Asymmetric Synthesis of Three‐Membered Carbocycles

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Ghanem

2014

Chirality

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“…With the equipment available for this study, the exact positions of the substituents at the aromatic rings could not be allocated. However, the most reactive sites (referring to the highest electron density, and over-all charge delocalization in the radical cations) are known from the literature [12,16,20,21], according to which the structures in Fig. 5 are drawn.…”

Section: Mechanistic Studiesmentioning

confidence: 99%

“…Extensive studies have been carried out with respect to their electrochemical oxidation under various conditions [20,21]. As their liquid chromatographic separation has been carried out for a long time [22], the current study was undertaken to evaluate the possibilities of LC-EC-MS investigations on PAH.…”

Section: Introductionmentioning

confidence: 99%

Liquid chromatography–electrochemistry–mass spectrometry of polycyclic aromatic hydrocarbons

2003

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An efficient method for fast elucidation of the electrochemical reactions of polycyclic aromatic hydrocarbons (PAH) has been set up by applying post-column electrochemistry in liquid chromatography-mass spectrometry (LC-MS). With this set-up strong improvement of sensitivity in the LC-MS analysis of PAH is observed. Due to their low redox potentials, the non-polar PAH are converted into the respective radical cations, which may further react with constituents of the mobile phase and in additional electrochemical oxidation steps. Among other products, mono-, di-, and trioxygenated species are observed in aqueous solutions, alkoxylated compounds in alcohols, and solvent adducts in the presence of acetonitrile. While more different products are observed by using atmospheric pressure chemical ionization in the positive-ion mode (APCI(+)), the deprotonation of hydroxylated species results in very clear spectra in the negative-ion mode (APCI(-)). Deuterated PAH and deuterated solvents were used to gain additional information on the formation of the reaction products.

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“…Thus, ifj~is the fraction of pyrene which electropolymerizes, then (1 -J) is the fraction which forms soluble species, and the following relationship can be written n~pp = n J + n l l -~ [1] Thus, considering the above values, the fraction of pyrene which gives rise to polypyrene is 0.54, i.e., only half of the reaction yields polymer film during electro-oxidation. The separation of the first peak in the voltammogram for pyrene, which is not observed with the other compounds, may simply be due to smaller current ,levels for the film products due to their low yield.…”

Section: N=l Soluble Product N--2 ~ Polymermentioning

confidence: 99%